Flavanone derivatives

Abstract

New flavanone derivatives of the formula I ##STR1## wherein Ar 1 and Ar 2 are each phenyl which is unsubstituted or monosubstituted to trisubstituted by OH, alkyl, alkoxy, acylamino, halogen, COOalkyl and/or NO 2 and/or substituted by a methylenedioxy group, and the alkyl, alkoxy and acyl groups each have 1-7 C atoms, but wherein the HO group is only in the 6-position if at least one of the radicals Ar 1 and Ar 2 is substituted phenyl, and the phosphoric acid esters thereof and the salts of these compounds display antiallergic effects. Salts of the I-phosphoric acid esters with aminoglycoside antibiotics are outstandingly stable and possess advantageous kinetics of liberation.

We claim: 
     
       1. A flavanone of the formula ##STR6## wherein each of Ar 1  and Ar 2  independently is phenyl, or phenyl (a) monosubstituted to trisubstituted by OH, alkyl, alkoxy, alkanoylamino, halogen, COOalkyl, NO 2  or a combination thereof; (b) substituted by methylenedioxy; or (c) substituted as in (a) and (b); each alkyl, alkoxy and alkanoyl group is 1-7 C atoms,   with the proviso that the HO group on the benzofused ring is in the 6-position, only when at least one of Ar 1  and Ar 2  is substituted phenyl,   or a phosphoric acid ester thereof   or a pharmaceutically acceptable salt of the flavanone or phosphoric ester.   
     
     
       2. A flavanone of claim 1 wherein Ar 1  and Ar 2  are the same. 
     
     
       3. A flavanone of claim 1 wherein the 6-position is occupied by OH. 
     
     
       4. A flavanone of claim 1 wherein either Ar 1  or Ar 2  is phenyl or phenyl which is mono-substituted by OH, alkyl, alkoxy or alkanoylamino each of 1-4 C atoms, F, Cl, Br, I, COOalkyl wherein alkyl is of 1-4 C atoms, NO 2  or methylenedioxy, or disubstituted by alkoxy of 1-4 C atoms or by Cl, or trisubstituted by alkoxy of 1-4 C atoms. 
     
     
       5. A flavanone of claim 1 wherein either Ar 1  or Ar 2  is phenyl, isopropylphenyl, methoxyphenyl, acetamidophenyl, chlorophenyl, dichlorophenyl or trimethoxyphenyl; 
     
     
       6. A flavanone of claim 1 wherein either Ar 1  or Ar 2  is phenyl or methoxyphenyl. 
     
     
       7. A flavanone of claim 1 wherein either Ar 1  or Ar 2  is p-methoxyphenyl. 
     
     
       8. A flavanone of claim 1 wherein Ar 1  and Ar 2  are each phenyl or phenyl which is monosubstituted by OH, alkyl, alkoxy or alkanoylamino each of 1-4 C atoms, F, Cl, Br, I COOalkyl wherein alkyl is of 1-4 C atoms, NO 2  or methylenedioxy, or disubstituted by alkoxy of 1-4 C atoms or Cl, or trisubstituted by alkoxy of 1-4 C atoms. 
     
     
       9. A flavanone of claim 1 wherein Ar 1  and Ar 2  are each phenyl, isopropylphenyl, methoxyphenyl, acetamidophenyl, chlorophenyl, dichlorophenyl or trimethoxyphenyl. 
     
     
       10. A flavanone of claim 1 wherein Ar 1  and Ar 2  are each phenyl or methoxypheyl. 
     
     
       11. A flavanone of claim 1 wherein Ar 1  and Ar 2  are each p-methoxyphenyl. 
     
     
       12. A compound of claim 1 which is a phosphate. 
     
     
       13. A compound of claim 1 which is a pharmaceutically acceptable salt. 
     
     
       14. A compound of claim 12 which is a pharmaceutically acceptable salt. 
     
     
       15. The gentamycin salt of 3-p-methoxybenzylidene-6-hydroxy-4'-methoxyflavanone-6-phosphoric acid ester, a compound of claim 1. 
     
     
       16. A salt of claim 13 with an aminoglycoside antibiotic. 
     
     
       17. A salt of claim 14 with an aminoglycoside antiobiotic. 
     
     
       18. A pharmaceutical composition comprising an anti-allergically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier. 
     
     
       19. A composition of claim 18 wherein the amount of flavanone is 5-1000 mg. 
     
     
       20. A method of achieving an antiallergic effect comprising administering a compound of claim 1. 
     
     
       21. A method of achieving an antibiotic effect comprising administering a compound of claim 13 which is a salt of an aminoglycoside antibiotic. 
     
     
       22. A method of achieving an antibiotic and an antiallergic effect comprising administering a compound of claim 13 which is a salt of an aminoglycoside antibiotic. 
     
     
       23. A pharmaceutical composition comprising an antibiotically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier. 
     
     
       24. A composition of claim 23 wherein the amount of flavanone is 5-1000 mg.